Recent studies have demonstrated that the sugar chains of glycolipids and glycoproteins function as receptors of hormones, bacterial toxins, viruses and others and are profoundly involved in basic dynamic biological phenomena such as cell recognition, differentiation/proliferation, adhesion, transformation, immunity and aging.
Cell surface sugar chains, closely associated with blood group substances such as those of the ABO (H antigen), Lewis (Le antigen) and Ii blood types, are also detected as cancer-related sugar chain antigens. For this reason, there have been studies to apply monoclonal antibodies, that specifically recognize this series of sugar chains, to cancer diagnosis and treatment.
The sialyl Le type sugar chain antigen, a tetrasaccharide sugar chain antigen basically composed of .alpha.(2.fwdarw.3) sialyl and .alpha.(1.fwdarw.3 and 1.fwdarw.4) fucosylated lactosamine, and found in sialoglycoprotein sugar chains as well as in gangliosides, has been used in serologic diagnosis of cancer as a sugar chain antigen for pulmonary adenocarcinoma and digestive tract cancer. Also, sialyl Le.sup.x sugar chains have very recently been reported as functioning as sugar chain ligands for the leukocyte adhesion factor appearing on vascular endothelial cells during intimation [Lowe, J. B., et al., Cell, 63, 475-484 (1990)].
It is very difficult, however, to obtain these sugar chains as a pure single compound from the living body because they are present in the cell surface layer only in trace amounts.
Against this background various synthetic compounds, including derivatives, have been studied, but none have been known to have moranoline (1-deoxynojirimycin) as a sugar chain component like the compounds of the present invention.
The object of the present invention is to provide a sugar chain derivative that is useful as a pharmaceutical and has a new structure.